Excerpt: Uncovering the Sources of our Anxiety

Once you recognize that what you are experiencing is most likely anxiety, the question becomes how do you release the grip of anxiety so you can operate with expanded awareness and creativity?

Milano offers that the first step toward uncovering the source of your anxiety is to pay attention to your attachments to certain outcomes and identities. “Anxiety is the fear of more fear. It’s fueled by attachment. It is rooted in the need to control the things around us to keep our reality known and safe.” Milano suggests that founders suffering from anxiety walk themselves through these questions:

What expectation, idea, or outcome are you attached to? A specific investor? A specific client? A certain type of product working? Being cash positive in six months?

What identity is driving the attachment? Have you created an image of yourself as the next game-changing entrepreneur to investors, the press, and your team?

Consider this example: A founder tells her investors that the company will be cash positive in six months. Then inevitable obstacles set in, and it becomes clear that goal is unattainable. It would be easy to descend into a morass of anxiety and what-ifs: Will the board let me go? Will the team start questioning my leadership?

A leader who has practiced uncovering their attachments, on the other hand, can see things in a more productive way. “The healthy thing to do is acknowledge the attachment to a certain outcome, soften your grip on it, and use your creativity to design a new path based on reality,” says Milano. “You get to what's really true and face what's actually happening. Then you can say to your team, from a place of integrity and clear-headedness, ‘Looks like it won’t be six months. Looks more like 12 months. Now that we know that, here’s what we’re doing about it.’”

Attachment to identities can be harder to relinquish, but it’s critical to consider. Many founders, whether through their own strategy or the attention of the press, assume the mantle of “the next big thing.” Suddenly, they’re not just building a product and running a company, they’re living up to very public expectations. “Now if your product launch isn't working very well, it starts to threaten that identity. Not only is your product broken, but you’re a fraud, a common human fear.

That’s one of entrepreneurs’ biggest fears: I went out there, I sold all these friends and investors on the next big thing, and it didn’t work. I’m a fraud.

“What this speaks to is the power of humility,” says Milano. The most inspirational leaders know that it’s not about them. They acknowledge challenges and respect the competition, and they are prepared for ups and downs. And importantly, they communicate this to their team and investors. “They say, ‘This isn't about me. This is about all of us collectively working together to achieve this beautiful mission. We’re going to face some bumps along the way, and what’s important is we navigate them together, as a team and a board.’

Cordaro adds, “It’s important to know that it’s ok to have certain identities, it’s totally natural and part of being human. Just know that all these identities come with hidden expectations that can add up quickly. It’s much more pleasant to make decisions as a leader from a place of what’s best for the company and society, as opposed to maintaining a personal identity.”

Once Milano and Cordaro support their clients in identifying their unconscious attachments and identities, they go a few layers deeper into the three main sources of fear, which they call “the three cultures of fear.”

The Culture of Scarcity: The belief system that there’s not enough resources (e.g. time, money, etc.).

The Culture of Aversion: The belief system that says “I’m having the wrong experience,” or “I shouldn’t be feeling this emotion.” (e.g. shame, guilt, etc.)

The Culture of Unworthiness: The belief system that “I’m not enough, just the way I am.”

The Culture of Scarcity is familiar to most entrepreneurs who are often scraping by financially or working 16 hours per day to achieve the next big thing. In relation to time scarcity, Cordaro says, “What’s interesting is that Silicon Valley is one of the most abundant places on the planet in regards to financial resources, yet when it comes to time, it is one of the most impoverished places on the planet.”

Milano and Cordaro offer that the Culture of Scarcity is a myth, deeply rooted in unconscious societal programming that can be transformed with awareness and new habits. This practice is important according to Cordaro because “when scarcity dominates, selfishness, hypercompetition, and creative stagnancy do too. When abundance dominates, generosity, cooperation, and rapid transformation are there too.”

When working with clients, Milano and Cordaro take people deep into their individual scarcity programming to write new, more empowering stories for their lives.

Reject the Culture of Aversion

Cordaro notes that the goal should never be to eliminate fear, but rather to acknowledge and accept it. He sees the same pattern unfold with all the entrepreneurs he coaches: First comes a great idea, and the drive to make it a reality. “It's very exciting and really fun. It's very desire and creativity-driven.” Then they start actually building a company, and things get in the way — and anxiety sets in. “Now there are things that are getting in the way of my vision; there are things that are coming up against these visions I have for how I want the world to be. Fear is a natural part of this process.”

Adopt this mindset, and fear stops looking like a threat; it’s merely part of the package.

In Milano and Cordaro’s experience, the following shift in mindset can have a profound influence on founders. When a product fails, when the new app gets two stars in the App Store, when funding isn’t coming through, successful founders don’t get caught up thinking, “This is the wrong experience. This isn’t the way it’s supposed to be.” Instead, they accept those obstacles as part of their experience — the only one they can and should be having. They use the experience as a growth opportunity to become better, stronger, and more inspirational leaders.

“When your product isn’t working, you need that feedback in order to actually create a product that people do want,” says Milano.

“Every time you're experiencing fear and anxiety, there's information and data that wants to be uncovered.”

Anxiety lets you know when you need to kick into gear. The problem, Milano notes, is when you simply stew in anxiety all day, every day. These emotions will not serve you well if they become chronic. And where there is chronic anxiety, there is almost always avoidance or aversion.

That app with the two-star rating? Customers don’t like it — it needs to change. “The person with a healthy relationship with fear can say, ‘This is what's happening. I'm going to accept that, embrace that, and receive the information. Now what can I do creatively to solve this?’” says Milano. Leaders with an unhealthy relationship to fear, on the other hand, often lose the opportunity to course-correct. Stuck on how things “should” go, they miss the valuable signal that it’s time to pivot.

Moreover, avoiding feelings of fear only prolongs them. “All emotions are here to provide us with information about the world around us. That's why we've evolved to feel them. Emotions are data; they’ve helped us survive for tens of thousands of generations. If we're not listening to an emotion, if we're not receiving that data fully, it's going to keep coming,” says Cordaro. When you allow yourself to fully feel and accept an emotion, it dissipates very quickly, often in as little as 30 to 90 seconds.

Seen that way, accepting fear isn’t just a nice idea — it’s a serious competitive advantage. That broken product or low-rated app isn’t going to fix itself. But you can effectively halve all of your problems by listening to your fear and letting it go. Cordaro asks: “As an entrepreneur, do you want to double every single problem that you have, or do you just want to deal with the things that actually need to be worked on?”

Be an example for your team: Entrepreneurship is a roller coaster. Let’s accept that and fix what we can. There will be no freaking out.

Develop an Unshakeable Sense of Self Worth

The final culture of fear is the Culture of Unworthiness. “This one goes beyond entrepreneurship, it is an epidemic of the human species,” says Milano. The belief system is that “I’m not enough just the way I am, I need to achieve something extraordinary to generate fulfillment.” This is the culture that had hit Milano the hardest so many years ago.

Often when Milano asks his clients if they are looking to prove something to themselves, their family, or society by building their company, the answer is a quick, reactive ‘no.’ “Most people are not consciously aware of how powerful the Culture of Unworthiness is until they make a major mistake or ‘fail.’ I certainly wasn’t aware of it.”

Milano offers that one of the quickest ways to determine if you have some work to do around your own sense of worthiness is to ask yourself the question “If my company completely fails and I fall flat on my face, will I still love and accept myself unconditionally.” When Cordaro and Milano ask this question in their virtual group coaching sessions you can often see people stop breathing even through the video conferencing technology. "It’s a powerful and shaking experience," Milano says.

We live in an entrepreneurial culture that “glorifies entrepreneurs as modern gods,” says Cordaro. “We worship those who achieve impossible tasks and create things that few have only dreamed of, kind of like what Elon Musk is doing with electric vehicles and clean energy. These are extraordinary people, for sure, but when we pin all of our self-worth on becoming exactly like them, however, we’re asking for trouble.”

“When we are faced with the loss of our dreams and ideals, a natural response is a feeling of low self worth,” says Milano. For him, this was the greatest gift of his food waste startup failure.

“Through that experience I was forced to marinate in my feelings of failure and low self worth, and learn the vitally important lesson that no success and achievement will ever fill the gap of self worth within," he says. "No expensive houses, shiny cars, or flashy press headlines will ever provide true fulfillment. I am now experiencing what it feels like to be of service and create for the sheer joy of it, without the requirement for my company to validate my self worth. In my opinion, this is one of the most important skill sets an entrepreneur can cultivate.”

Through that experience, Milano now leads his clients into their unique personal experiences that are the sources of their Culture of Unworthiness. “Maybe your parents didn’t tell you that you were good enough, and you’re trying to prove that you’re worthy,” he says. Other times, the sabotaging hang-ups are professional in nature — the traumatic experience of having been fired as CEO is a prime example, and now you want to prove you can be CEO.”

In Cordaro’s experience as a psychologist, learning to conduct this sort of self-enquiry can be transformative for founders. “One of the most powerful things that I've seen people do is simply develop a curiosity about who they are and why they behave the way that they do,” he says. “It’s that kind of attitude that allows people to be the most impactful they can possibly be in society.”